EP2415470B1 - Liposome composition - Google Patents

Liposome composition Download PDF

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Publication number
EP2415470B1
EP2415470B1 EP10758755.2A EP10758755A EP2415470B1 EP 2415470 B1 EP2415470 B1 EP 2415470B1 EP 10758755 A EP10758755 A EP 10758755A EP 2415470 B1 EP2415470 B1 EP 2415470B1
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EP
European Patent Office
Prior art keywords
liposome
composition according
external phase
phase
dispersion liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP10758755.2A
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German (de)
English (en)
French (fr)
Other versions
EP2415470A4 (en
EP2415470A1 (en
Inventor
Hiroshi Kikuchi
Kenji Hyodo
Hiroshi Ishihara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eisai R&D Management Co Ltd
Original Assignee
Eisai R&D Management Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
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Application filed by Eisai R&D Management Co Ltd filed Critical Eisai R&D Management Co Ltd
Priority to MEP-2016-188A priority Critical patent/ME02518B/me
Priority to SI201031275A priority patent/SI2415470T1/sl
Priority to RS20160763A priority patent/RS55148B1/sr
Publication of EP2415470A1 publication Critical patent/EP2415470A1/en
Publication of EP2415470A4 publication Critical patent/EP2415470A4/en
Application granted granted Critical
Publication of EP2415470B1 publication Critical patent/EP2415470B1/en
Priority to HRP20161157TT priority patent/HRP20161157T1/hr
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Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1277—Processes for preparing; Proliposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1277—Processes for preparing; Proliposomes
    • A61K9/1278—Post-loading, e.g. by ion or pH gradient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • Liposome internal phase means an aqueous region enclosed in the lipid bilayer of the liposome, and is used with the same meaning as “internal water phase” and “liposome internal water phase.”
  • “Liposome external phase” means the region not enclosed by the lipid bilayer of the liposome (that is, the region apart from the internal phase and the lipid bilayer) in the case where the liposome is dispersed in liquid.
  • anti-inflammatory agents there are no particular limitions on anti-inflammatory agents, and one may cite, for example, prostaglandins (PGE1, PGE2), dexamethasone, hydrocortisone, pyroxicam, indomethacin, prednisolone, etc. With respect to compounds of the aforementioned anti-inflammatory agents, any salt is acceptable.
  • temperature-sensitive lipid derivatives one may cite, for example, dipalmitoyl phosphatidylcholine, etc.
  • the liposome By having the liposome contain temperature-sensitive lipid derivatives, it is possible to cause destruction of liposome at specific temperatures, and cause changes in the surface properties of the liposome. Furthermore, by combining this with an increase in temperature at the target site of the tumor, etc., it is possible to destroy the liposome at the target site, and release the active compound at the target site.
  • the liposome composition be targeted to target tissue such as solid cancer, but it can also be used to transmit active compounds to hematological cancer and so on. It can also be used as a slow release formulation, controlled release formulation, etc. in blood.
  • the concentration of liposome and the concentration of the active compound in the liposome composition can be appropriately set according to the liposome composition objective, formulation, etc.
  • the concentration of liposome as the concentration of all lipids constituting the liposome may be set at 0.2 to 100 mM, and preferably at 1 to 30 mM.
  • the concentration (dosage) of active compound in the case where the liposome composition is used as a medicine is described below.
  • the quantity of cyclodextrin in the liposome composition it is preferable that it be less than a 0.1 mol equivalent relative to the eribulin, etc., and it is more preferable that it be less than the limit of detection.
  • the liposome dispersion liquid can be obtained by substituting or diluting the external phase of the obtained liposome preparatory solution.
  • the substitution or dilution of the liposome external phase may be conducted once, or a combination of various types of substitution or dilution methods may be conducted multiple times.
  • Those skilled in the art may set the quantity of membrane fluidizer according to the composition of liposome membrane constituents, the membrane fluidizer, etc., and taking into consideration the degree of efficiency of entrapment of the active compound due to addition of the membrane fluidizer, the stability of the liposome, etc.
  • Eribulin mesylate (eribulin mesylate) was dissolved in the 0.9% sodium chloride/10 mM histidine aqueous solution and 5 mg/mL eribulin mesylate solution was obtained.
  • a tumor-reducing effect was not obtained even at 4 mg/kg, which is the maximum tolerated dose for free bodies, because FaDu is a cell line with a low sensitivity to eribulin mesylate.
  • FaDu is a cell line with a low sensitivity to eribulin mesylate.
  • a clear tumor-reducing effect was found even with the administration of 2 mg/kg, which is below the maximum tolerance dose, indicating that an extremely high pharmacological effect can be obtained even for types of cancers against which there has been no success with eribulin mesylate.
  • Calipers were used to measure the tumor size over time, and the tumor size was calculated based on the calculation formula: major axis ⁇ (minor axis squared) ⁇ 2.
  • major axis ⁇ minor axis squared
  • the mice were separated into groups such that the average values of the tumor sizes and the body weights of mice were uniform among the test groups (five mice per test group), and the drug was administered into the caudal vein (0.2 mL/20 g; 3 times in 7-day intervals).
  • the obtained liposome preparatory liquid was eluted with 0.9% sodium chloride/10 mM histidine aqueous solution, substituting the liposome external phase with the 0.9% sodium chloride/10 mM histidine aqueous solution.
  • the liposome dispersion liquid and the eribulin mesylate solution were mixed in a 10-mL glass vessel such that the eribulin mesylate was 0.2 mg/mL and the total lipid concentration was 16 mM. This was heated for 5 minutes at 60° C to obtain a liposome composition with eribulin mesylate introduced into the liposomes.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
EP10758755.2A 2009-03-30 2010-03-30 Liposome composition Active EP2415470B1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MEP-2016-188A ME02518B (me) 2009-03-30 2010-03-30 Smeša lipozoma
SI201031275A SI2415470T1 (sl) 2009-03-30 2010-03-30 Liposomski sestavek
RS20160763A RS55148B1 (sr) 2009-03-30 2010-03-30 Smeša lipozoma
HRP20161157TT HRP20161157T1 (hr) 2009-03-30 2016-09-08 Liposomski pripravak

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16465309P 2009-03-30 2009-03-30
JP2009082521 2009-03-30
PCT/JP2010/055770 WO2010113984A1 (ja) 2009-03-30 2010-03-30 リポソーム組成物

Publications (3)

Publication Number Publication Date
EP2415470A1 EP2415470A1 (en) 2012-02-08
EP2415470A4 EP2415470A4 (en) 2012-11-28
EP2415470B1 true EP2415470B1 (en) 2016-07-06

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ID=42828273

Family Applications (1)

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EP10758755.2A Active EP2415470B1 (en) 2009-03-30 2010-03-30 Liposome composition

Country Status (33)

Country Link
US (3) US20120058178A1 (es)
EP (1) EP2415470B1 (es)
JP (1) JP5551683B2 (es)
KR (1) KR101495951B1 (es)
CN (1) CN102369008B (es)
AU (1) AU2010232347A1 (es)
BR (1) BRPI1014527B8 (es)
CA (1) CA2756811C (es)
CO (1) CO6430500A2 (es)
CY (1) CY1118231T1 (es)
DK (1) DK2415470T3 (es)
ES (1) ES2593027T3 (es)
HK (1) HK1165707A1 (es)
HR (1) HRP20161157T1 (es)
HU (1) HUE029577T2 (es)
IL (1) IL215059A (es)
LT (1) LT2415470T (es)
MA (1) MA33127B1 (es)
ME (1) ME02518B (es)
MX (1) MX2011009632A (es)
MY (1) MY160203A (es)
NZ (1) NZ595212A (es)
PE (2) PE20151519A1 (es)
PL (1) PL2415470T3 (es)
PT (1) PT2415470T (es)
RS (1) RS55148B1 (es)
SG (1) SG174255A1 (es)
SI (1) SI2415470T1 (es)
SM (1) SMT201600307B (es)
TW (1) TWI392519B (es)
UA (1) UA103794C2 (es)
WO (1) WO2010113984A1 (es)
ZA (1) ZA201106535B (es)

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CA2756811C (en) 2014-09-23
KR20110122219A (ko) 2011-11-09
UA103794C2 (en) 2013-11-25
MX2011009632A (es) 2011-10-19
US20140044777A1 (en) 2014-02-13
JP5551683B2 (ja) 2014-07-16
ES2593027T3 (es) 2016-12-05
RS55148B1 (sr) 2016-12-30
SMT201600307B (it) 2016-11-10
BRPI1014527A2 (pt) 2016-04-05
CA2756811A1 (en) 2010-10-07
ME02518B (me) 2017-02-20
PL2415470T3 (pl) 2016-12-30
PE20151519A1 (es) 2015-10-28
US11071713B2 (en) 2021-07-27
CN102369008A (zh) 2012-03-07
US20210023004A1 (en) 2021-01-28
EP2415470A4 (en) 2012-11-28
US12042560B2 (en) 2024-07-23
TW201102110A (en) 2011-01-16
BRPI1014527B1 (pt) 2020-11-24
KR101495951B1 (ko) 2015-02-25
DK2415470T3 (en) 2016-09-19
HK1165707A1 (zh) 2012-10-12
HUE029577T2 (en) 2017-03-28
SI2415470T1 (sl) 2016-12-30
HRP20161157T1 (hr) 2016-11-18
NZ595212A (en) 2014-02-28
AU2010232347A1 (en) 2011-09-29
SG174255A1 (en) 2011-10-28
BRPI1014527B8 (pt) 2021-05-25
IL215059A0 (en) 2011-11-30
ZA201106535B (en) 2012-05-30
MY160203A (en) 2017-02-28
JPWO2010113984A1 (ja) 2012-10-11
MA33127B1 (fr) 2012-03-01
PT2415470T (pt) 2016-08-31
WO2010113984A1 (ja) 2010-10-07
CN102369008B (zh) 2014-10-29
US20120058178A1 (en) 2012-03-08
EP2415470A1 (en) 2012-02-08
LT2415470T (lt) 2016-10-10
CY1118231T1 (el) 2017-06-28
PE20120923A1 (es) 2012-08-27
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